Stereoselective synthesis of novel dipeptide β-turn mimetics targeting melanocortin peptide receptors

Junyi Zhang, Chiyi Xiong, Jinfa Ying, Wei Wang, Victor J Hruby

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

(Matrix presented) The novel dipeptide β-turn mimetic, 4,8-disubstituted azabicyclo[4.3.0]nonane amino acid ester (15), has been synthesized to serve as a peptide mimetic of the dipeptide Phe-Arg, which contains two important pharmacophore elements in melanotropin peptides. Introduction of side-chain functionality at C-8 was achieved by using β-functionalized pyroglutamate (8) as a synthetic precursor. The side chain at C-4 was introduced by bromination of dehydroamino acid intermediate (10) followed by Suzuki cross-coupling.

Original languageEnglish (US)
Pages (from-to)3115-3118
Number of pages4
JournalOrganic Letters
Volume5
Issue number17
DOIs
StatePublished - Aug 21 2003

Fingerprint

Melanocortin Receptors
Melanocortins
Peptide Receptors
Dipeptides
peptides
Azabicyclo Compounds
phenylalanylarginine
Pyrrolidonecarboxylic Acid
Melanocyte-Stimulating Hormones
bromination
nonanes
Peptides
Halogenation
cross coupling
synthesis
amino acids
esters
Esters
Amino Acids
acids

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Stereoselective synthesis of novel dipeptide β-turn mimetics targeting melanocortin peptide receptors. / Zhang, Junyi; Xiong, Chiyi; Ying, Jinfa; Wang, Wei; Hruby, Victor J.

In: Organic Letters, Vol. 5, No. 17, 21.08.2003, p. 3115-3118.

Research output: Contribution to journalArticle

Zhang, Junyi ; Xiong, Chiyi ; Ying, Jinfa ; Wang, Wei ; Hruby, Victor J. / Stereoselective synthesis of novel dipeptide β-turn mimetics targeting melanocortin peptide receptors. In: Organic Letters. 2003 ; Vol. 5, No. 17. pp. 3115-3118.
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